Trifluoroacetic acid → HCID 69895619, compound

HRID 1385786Notes

Reaction equation

HRID 1385786 reaction equation
C([O:5][C:6]([C@H:8]1[CH2:12][CH2:11][CH2:10][N:9]1[C:13](=[O:35])[CH2:14][CH2:15][N:16]([CH2:19][CH2:20][C:21]([N:23]1[CH2:27][CH2:26][CH2:25][C@@H:24]1[C:28]([O:30]C(C)(C)C)=[O:29])=[O:22])[CH2:17][CH3:18])=[O:7])(C)(C)C.[F:36][C:37]([F:42])([F:41])[C:38]([OH:40])=[O:39]>ClCCl.O>[F:36][C:37]([F:42])([F:41])[C:38]([OH:40])=[O:39].[CH2:17]([N:16]([CH2:15][CH2:14][C:13]([N:9]1[CH2:10][CH2:11][CH2:12][C@@H:8]1[C:6]([OH:7])=[O:5])=[O:35])[CH2:19][CH2:20][C:21]([N:23]1[CH2:27][CH2:26][CH2:25][C@@H:24]1[C:28]([OH:30])=[O:29])=[O:22])[CH3:18]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54399255HCID 54399255, compound

Product 1

HCID 69895619HCID 69895619, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 85 mg (0.17 mmol) (R)-1-[3-[[3-[(R)-2-tert-butoxycarbonyl-pyrrolidin-1-yl]-3-oxo-propyl]-ethyl-amino]-propionyl]-pyrrolidine-2-carboxylic acid tert-butyl ester in 5 ml dichloromethane at 0° C. was added dropwise 1.0 ml trifluoroacetic acid and stirring continued for 16 h at room temperature. Concentration in vacuo and azeotroping three times with chloroform on a rotary evaporator afforded, after resuspension in water and lyophilization, 63 mg (97%) of the title compound as a yellow crystalline solid. MS m/e (%): 442 ([M+OAc]31 , 35), 382 ([M−H]−, 100).

Workup

  1. concentrationConcentration in vacuo
  2. customazeotroping three times with chloroform
  3. customon a rotary evaporator
  4. customafforded

Sources & evidence

ORD record
ord-88914185031647b79d1ba66c41fa518f
Source dataset
uspto-grants-2001_07
Patent number
US06262089B1

Reaction notes

Loading…